Diisopropylethylamine → N-benzyl-2-(1-(4-fluorophenethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxamide

HRID 2381800Notes

Reaction equation

HRID 2381800 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]#[CH:17])=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[N:28]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)=[N+:29]=[N-:30]>O1CCCC1.[Cu]I>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[N:30]=[N:29][N:28]([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[CH:17]=2)=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 596674281-(2-Azidoethyl)-4-fluorobenzeneHCID 73213266N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide

Product 1

HCID 24962976N-benzyl-2-(1-(4-fluorophenethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxamideYield 55%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide (0.10 g, 0.39 mmol) in tetrahydrofuran (5 mL) was added copper(I) iodide (0.002 g, 0.008 mmol), N,N-diisopropylethylamine (0.082 mL, 0.47 mmol) and 1-(2-azidoethyl)-4-fluorobenzene (0.077 g, 0.47 mmol). The reaction mixture was stirred at ambient temperature for 17 hours then concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:hexanes, 1:1) to afford the title compound as a white solid (0.090 g, 55%): mp 181-182° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.84 (s, 1H), 7.38-7.24 (m, 5H), 7.09-6.99 (m, 2H), 6.95-6.85 (m, 2H), 6.23 (t, J=5.6 Hz, 1H), 4.61-4.56 (m, 4H), 3.20 (t, J=7.1 Hz, 2H), 2.67 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.9, 161.6, 157.9, 156.7, 142.5, 137.8, 132.2, 130.1, 128.8, 127.8, 127.7, 124.8, 121.8, 115.9, 52.0, 44.2, 35.7, 17.3; MS (ES+) m/z 422.3 (M+1).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by column chromatography (ethyl acetate:hexanes, 1:1)

Sources & evidence

ORD record
ord-c844770a7f8e4447be299ae11154d38f
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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